620-26-8

Basic information

• Product Name: m-nitrosotoluene
• Synonyms: m-nitrosotoluene;META-NITROSOTOLUENE;1-methyl-3-nitrosobenzene;1-methyl-3-nitroso-benzene;Benzene, 1-Methyl-3-nitroso-
• CAS NO: 620-26-8
• Molecular Formula: C₇H₇NO
• Molecular Weight: 121.13658
• EINECS: 210-634-1
• Mol File: 620-26-8.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 204.1°C at 760 mmHg
• Flash Point: 76.8°C
• Appearance: /
• Density: 1.03g/cm³
• Vapor Pressure: 0.383mmHg at 25°C
• Refractive Index: 1.524
• CAS DataBase Reference: m-nitrosotoluene(CAS DataBase Reference)
• NIST Chemistry Reference: m-nitrosotoluene(620-26-8)
• EPA Substance Registry System: m-nitrosotoluene(620-26-8)

Safety Data

• Hazardous Substances Data: 620-26-8(Hazardous Substances Data)

Usage

General Description

M-nitrosotoluene is an organic compound with the chemical formula C7H7NO. It is a colorless to pale yellow liquid with a musty odor, and is classified as a nitrosamine, a group of chemical compounds known to have carcinogenic properties. M-nitrosotoluene is primarily used as an intermediate in the production of various organic compounds and polymers, and it is also used in the manufacturing of dyes and pharmaceuticals. The compound is considered to be hazardous, as exposure to m-nitrosotoluene can cause irritation to the respiratory system and skin, and prolonged or high-level exposure can lead to more serious health effects. As a result, proper precautions and safety measures should be taken when handling or working with m-nitrosotoluene.

InChI:InChI=1/C7H7NO/c1-6-3-2-4-7(5-6)8-9/h2-5H,1H3

Upstream product

• 108-44-1 1-amino-3-methylbenzene 
• 82860-26-2 Di-m-tolyl-diazene N,N'-dioxide 
• 99-08-1 1-methyl-3-nitrobenzene 
• 82860-26-2 (Z)-di-m-tolyl-diazene-N,N'-dioxide 
• 620-25-7 N-(3-methylphenyl)hydroxylamine 
• 937-01-9 trimethyl(3-methylphenyl)stannane 

Downstream Products

• 71297-97-7 N,N'-bis(3-methylphenyl)-diazene N-oxide 
• 861044-22-6 2,4-dinitro-benzaldehyde-(N-m-tolyl oxime ) 
• 19618-06-5 (E)-di-m-tolyl-diazene-N-oxide 
• 92022-24-7 (4-bromo-phenyl)-m-tolyl-diazene 
• 27687-62-3 N-(3-methylphenyl)acetohydroxamic acid 

Relevant articles and documents

"Photo-Rimonabant": Synthesis and Biological Evaluation of Novel Photoswitchable Molecules Derived from Rimonabant Lead to a Highly Selective and Nanomolar " Cis-On" CB1R Antagonist

Human cannabinoid receptor type 1 (hCB1R) plays important roles in the regulation of appetite and development of addictive behaviors. Herein, we describe the design, synthesis, photocharacterization, molecular docking, and in vitro characterization of "photo-rimonabant", i.e., azo-derivatives of the selective hCB1R antagonist SR1411716A (rimonabant). By applying azo-extension strategies, we yielded compound 16a, which shows marked affinity for CB1R (Ki (cis form) = 29 nM), whose potency increases by illumination with ultraviolet light (CB1R Kitrans/cis ratio = 15.3). Through radioligand binding, calcium mobilization, and cell luminescence assays, we established that 16a is highly selective for hCB1R over hCB2R. These selective antagonists can be valuable molecular tools for optical modulation of CBRs and better understanding of disorders associated with the endocannabinoid system.

Reversible Photoswitchable Inhibitors Generate Ultrasensitivity in Out-of-Equilibrium Enzymatic Reactions

Ultrasensitivity is a ubiquitous emergent property of biochemical reaction networks. The design and construction of synthetic reaction networks exhibiting ultrasensitivity has been challenging, but would greatly expand the potential properties of life-like materials. Herein, we exploit a general and modular strategy to reversibly regulate the activity of enzymes using light and show how ultrasensitivity arises in simple out-of-equilibrium enzymatic systems upon incorporation of reversible photoswitchable inhibitors (PIs). Utilizing a chromophore/warhead strategy, PIs of the protease α-chymotrypsin were synthesized, which led to the discovery of inhibitors with large differences in inhibition constants (Ki) for the different photoisomers. A microfluidic flow setup was used to study enzymatic reactions under out-of-equilibrium conditions by continuous addition and removal of reagents. Upon irradiation of the continuously stirred tank reactor with different light pulse sequences, i.e., varying the pulse duration or frequency of UV and blue light irradiation, reversible switching between photoisomers resulted in ultrasensitive responses in enzymatic activity as well as frequency filtering of input signals. This general and modular strategy enables reversible and tunable control over the kinetic rates of individual enzyme-catalyzed reactions and makes a programmable linkage of enzymes to a wide range of network topologies feasible.

A Photoswitchable Agonist for the Histamine H3 Receptor, a Prototypic Family A G-Protein-Coupled Receptor

Spatiotemporal control over biochemical signaling processes involving G protein-coupled receptors (GPCRs) is highly desired for dissecting their complex intracellular signaling. We developed sixteen photoswitchable ligands for the human histamine H3 receptor (hH3R). Upon illumination, key compound 65 decreases its affinity for the hH3R by 8.5-fold and its potency in hH3R-mediated Gi protein activation by over 20-fold, with the trans and cis isomer both acting as full agonist. In real-time two-electrode voltage clamp experiments in Xenopus oocytes, 65 shows rapid light-induced modulation of hH3R activity. Ligand 65 shows good binding selectivity amongst the histamine receptor subfamily and has good photolytic stability. In all, 65 (VUF15000) is the first photoswitchable GPCR agonist confirmed to be modulated through its affinity and potency upon photoswitching while maintaining its intrinsic activity, rendering it a new chemical biology tool for spatiotemporal control of GPCR activation.